13. Wicker Park
Notable Businesses: The Bedford, Big Star, The Wormhole, Penelope's, Myopic Books, Reckless Records
Don't hold Paul McGuigan's cheesy 2004 film against the area, beacuse this northwest Chicago neighborhood is nothing like the eponymous flick. The neighborhood has been going through changes recently, with an increase in new restaurants, bars, and stores. The Bedford, located inside a bank vault, is worth checking out. There's a healthy mixture of vintage shops, record stores, and boutiques in addition to national chains. It's quickly become one of Chicago's most fashionable areas, beginning with the Milwaukee-Damen-North triangle. We particularly dig Penelope's, where you can pick up brands like A.P.C., GANT Rugger, and Our Legacy. Wicker Park has plenty of notable residents, like former Smashing Pumpkins guitarist James Iha, and aside from the film Wicker Park, it was also used as the setting for High Fidelity, starring Illinois-native John Cusack.